Acetone → 1,2:3,4:5,6-Tris-O-(1-methylethylidene)hexitol

HRID 358139

反応式

HRID 358139 の反応式
[CH3:1][C:2]([CH3:4])=[O:3].[CH2:5]([OH:16])[C@H:6]([C@H:8]([C@@H:10]([C@@H:12]([CH2:14]O)[OH:13])[OH:11])[OH:9])[OH:7].I>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:4])[O:13][CH:12]([CH:10]2[O:11][C:6]([CH3:8])([CH3:5])[O:9][CH:8]2[CH:6]2[O:7][C:12]([CH3:14])([CH3:10])[O:16][CH2:5]2)[CH2:14][O:3]1

参加物

5

反応物 3

HCID 180AcetoneHCID 6251MannitolHCID 24841Hydrogen iodide

生成物 1

HCID 3165221,2:3,4:5,6-Tris-O-(1-methylethylidene)hexitol収率 90%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
60 °C

実験手順

To 200 ml of acetone were added 10.0 g of D-mannitol and 175 mg of hydriodic acid (57%) and the mixture was refluxed with stirring in a water bath at 60° C. for 5 hours. During this reaction, the refluxing solvent was dried with 20 g of Molecular Sieves 3A interposed between the reaction vessel and the cooling jacket. After completion of the reaction, a small amount of pyridine was added. The acetone was then distilled off under reduced pressure and the residue was dissolved in chloroform. The solution was washed with aqueous sodium bicarbonate and water and dried over anhydrous magnesium sulfate. The chloroform was distilled off under reduced pressure to give 15.0 g (90%) of 1,2:3,4:5,6-tri-O-isopropylidene-D-mannitol. After recrystallization from 70% ethanol, it melted at 68.5°-70.5° C.

後処理

  1. temperaturethe mixture was refluxed
  2. customDuring this reaction
  3. dry with materialthe refluxing solvent was dried with 20 g of Molecular Sieves 3A
  4. customAfter completion of the reaction
  5. distillationThe acetone was then distilled off under reduced pressure
  6. dissolutionthe residue was dissolved in chloroform
  7. washThe solution was washed with aqueous sodium bicarbonate and water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe chloroform was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-5304b814bb924040bed5fe66f3dbb0bb
出典データセット
uspto-grants-1984_08
特許番号
US04464530

関連ノート

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